Efficient conversion of carbohydrates into 1-C-alditols: application to the synthesis of chiral gamma-substituted butenolides and bicyclic alkaloid analogues.

Readily available sugar derivatives were transformed in a few steps into valuable, more complex products. The tandem radical scission of carbohydrates-oxidation reaction gave acetoxy acetals, which were converted into a variety of chiral C-alditols in good global yields and excellent 1,2-trans stereoselectivity. The reaction was the key step in the synthesis of hydroxylated gamma-substituted butenolides and bicyclic alkaloid analogues.